# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd1284a
_database_code_depnum_ccdc_archive 'CCDC 1037965'
_audit_update_record             
;
2014-12-07 deposited with the CCDC.
2015-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        "8,8'-Biquinoline 1,1'-dioxide"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 N2 O2'
_chemical_formula_sum            'C18 H12 N2 O2'
_chemical_formula_weight         288.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.720(5)
_cell_length_b                   21.073(12)
_cell_length_c                   8.161(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.202(10)
_cell_angle_gamma                90.00
_cell_volume                     1326.7(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    98(2)
_cell_measurement_reflns_used    5938
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      40.2

_exptl_crystal_description       platelet
_exptl_crystal_colour            gold
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      98(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        <1
_diffrn_reflns_number            8790
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_reduction_process 'Lp corrections applied'
_reflns_number_total             2464
_reflns_number_gt                2132
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0380P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2464
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.33714(19) 0.17530(7) 0.65901(18) 0.0211(3) Uani 1 1 d . . .
O2 O 0.26749(17) 0.13087(6) 0.56563(15) 0.0249(3) Uani 1 1 d . . .
N1 N -0.0737(2) 0.11989(7) 0.76078(19) 0.0246(4) Uani 1 1 d . . .
C18 C 0.3543(2) 0.16577(8) 0.8281(2) 0.0215(4) Uani 1 1 d . . .
O1 O -0.00136(18) 0.17001(6) 0.82593(18) 0.0311(3) Uani 1 1 d . . .
C10 C 0.2919(2) 0.10954(9) 0.9029(2) 0.0223(4) Uani 1 1 d . . .
C8 C 0.1900(2) 0.05690(9) 0.8219(2) 0.0231(4) Uani 1 1 d . . .
C9 C 0.0167(2) 0.06195(9) 0.7584(2) 0.0225(4) Uani 1 1 d . . .
C4 C -0.0728(2) 0.00814(9) 0.6938(2) 0.0245(4) Uani 1 1 d . . .
C14 C 0.4392(2) 0.21371(9) 0.9239(2) 0.0248(4) Uani 1 1 d . . .
C1 C -0.2364(3) 0.12438(10) 0.6986(3) 0.0292(4) Uani 1 1 d . . .
C6 C 0.1753(3) -0.05721(9) 0.7661(3) 0.0304(5) Uani 1 1 d . . .
C5 C 0.0121(3) -0.05170(9) 0.6983(2) 0.0279(4) Uani 1 1 d . . .
C17 C 0.3946(2) 0.22913(9) 0.5913(2) 0.0253(4) Uani 1 1 d . . .
C7 C 0.2634(3) -0.00302(9) 0.8265(3) 0.0281(4) Uani 1 1 d . . .
C16 C 0.4750(3) 0.27702(9) 0.6845(3) 0.0294(5) Uani 1 1 d . . .
C11 C 0.3295(2) 0.10174(9) 1.0675(2) 0.0268(4) Uani 1 1 d . . .
C15 C 0.4973(3) 0.26994(9) 0.8492(3) 0.0288(4) Uani 1 1 d . . .
C3 C -0.2446(3) 0.01404(10) 0.6282(2) 0.0288(4) Uani 1 1 d . . .
C12 C 0.4151(3) 0.14840(10) 1.1637(2) 0.0290(4) Uani 1 1 d . . .
C2 C -0.3249(3) 0.07174(10) 0.6319(3) 0.0313(5) Uani 1 1 d . . .
C13 C 0.4659(3) 0.20369(10) 1.0947(2) 0.0290(4) Uani 1 1 d . . .
H17A H 0.377(3) 0.2324(10) 0.473(3) 0.035 Uiso 1 1 d . . .
H11A H 0.285(3) 0.0617(11) 1.122(3) 0.035 Uiso 1 1 d . . .
H16A H 0.517(3) 0.3118(11) 0.628(3) 0.035 Uiso 1 1 d . . .
H5A H -0.052(3) -0.0864(11) 0.645(3) 0.035 Uiso 1 1 d . . .
H1A H -0.283(3) 0.1707(11) 0.708(3) 0.035 Uiso 1 1 d . . .
H2A H -0.441(3) 0.0771(11) 0.592(3) 0.035 Uiso 1 1 d . . .
H12A H 0.427(3) 0.1423(10) 1.276(3) 0.035 Uiso 1 1 d . . .
H3A H -0.303(3) -0.0197(11) 0.574(3) 0.035 Uiso 1 1 d . . .
H15A H 0.557(3) 0.3007(11) 0.917(3) 0.035 Uiso 1 1 d . . .
H7A H 0.369(3) -0.0072(11) 0.867(3) 0.035 Uiso 1 1 d . . .
H13A H 0.522(3) 0.2382(11) 1.161(3) 0.035 Uiso 1 1 d . . .
H6A H 0.235(3) -0.0973(11) 0.767(3) 0.035 Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 O2 1.3095(19) . ?
N2 C17 1.345(2) . ?
N2 C18 1.396(2) . ?
N1 O1 1.299(2) . ?
N1 C1 1.339(3) . ?
N1 C9 1.407(2) . ?
C18 C14 1.422(3) . ?
C18 C10 1.425(3) . ?
C10 C11 1.374(3) . ?
C10 C8 1.498(3) . ?
C8 C7 1.384(3) . ?
C8 C9 1.420(3) . ?
C9 C4 1.419(3) . ?
C4 C3 1.416(3) . ?
C4 C5 1.421(3) . ?
C14 C15 1.413(3) . ?
C14 C13 1.417(3) . ?
C1 C2 1.402(3) . ?
C1 H1A 1.04(2) . ?
C6 C5 1.362(3) . ?
C6 C7 1.408(3) . ?
C6 H6A 0.96(2) . ?
C5 H5A 0.97(2) . ?
C17 C16 1.395(3) . ?
C17 H17A 0.97(2) . ?
C7 H7A 0.87(2) . ?
C16 C15 1.357(3) . ?
C16 H16A 0.93(2) . ?
C11 C12 1.407(3) . ?
C11 H11A 1.02(2) . ?
C15 H15A 0.96(2) . ?
C3 C2 1.366(3) . ?
C3 H3A 0.95(2) . ?
C12 C13 1.359(3) . ?
C12 H12A 0.92(2) . ?
C2 H2A 0.95(2) . ?
C13 H13A 0.99(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N2 C17 119.89(16) . . ?
O2 N2 C18 119.60(15) . . ?
C17 N2 C18 120.50(15) . . ?
O1 N1 C1 118.67(15) . . ?
O1 N1 C9 120.33(15) . . ?
C1 N1 C9 120.99(16) . . ?
N2 C18 C14 117.75(16) . . ?
N2 C18 C10 121.48(16) . . ?
C14 C18 C10 120.76(17) . . ?
C11 C10 C18 117.14(17) . . ?
C11 C10 C8 115.49(17) . . ?
C18 C10 C8 127.37(17) . . ?
C7 C8 C9 117.20(17) . . ?
C7 C8 C10 117.15(17) . . ?
C9 C8 C10 125.21(16) . . ?
N1 C9 C4 117.60(17) . . ?
N1 C9 C8 121.41(16) . . ?
C4 C9 C8 120.97(17) . . ?
C3 C4 C9 120.40(18) . . ?
C3 C4 C5 120.78(18) . . ?
C9 C4 C5 118.81(18) . . ?
C15 C14 C13 120.84(18) . . ?
C15 C14 C18 120.37(18) . . ?
C13 C14 C18 118.79(18) . . ?
N1 C1 C2 121.81(18) . . ?
N1 C1 H1A 111.0(13) . . ?
C2 C1 H1A 127.2(13) . . ?
C5 C6 C7 120.01(19) . . ?
C5 C6 H6A 120.9(14) . . ?
C7 C6 H6A 118.9(14) . . ?
C6 C5 C4 120.31(18) . . ?
C6 C5 H5A 124.1(13) . . ?
C4 C5 H5A 115.5(13) . . ?
N2 C17 C16 122.21(18) . . ?
N2 C17 H17A 115.6(13) . . ?
C16 C17 H17A 122.2(13) . . ?
C8 C7 C6 122.60(19) . . ?
C8 C7 H7A 118.4(15) . . ?
C6 C7 H7A 119.0(15) . . ?
C15 C16 C17 119.83(19) . . ?
C15 C16 H16A 122.7(14) . . ?
C17 C16 H16A 117.4(14) . . ?
C10 C11 C12 122.63(19) . . ?
C10 C11 H11A 117.6(13) . . ?
C12 C11 H11A 119.6(12) . . ?
C16 C15 C14 119.29(18) . . ?
C16 C15 H15A 122.5(13) . . ?
C14 C15 H15A 118.1(13) . . ?
C2 C3 C4 119.29(19) . . ?
C2 C3 H3A 118.0(14) . . ?
C4 C3 H3A 122.5(14) . . ?
C13 C12 C11 120.33(19) . . ?
C13 C12 H12A 120.6(14) . . ?
C11 C12 H12A 118.8(14) . . ?
C3 C2 C1 119.86(19) . . ?
C3 C2 H2A 121.5(14) . . ?
C1 C2 H2A 118.7(14) . . ?
C12 C13 C14 120.14(18) . . ?
C12 C13 H13A 121.9(13) . . ?
C14 C13 H13A 117.9(13) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.048
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Benzene, ethanol'
